Adam Sandler's latest comedy is shallow, scatological, lazy, crass and brazenly commercial. That's not news. But Jack and Jill may also mark something more significant: the moment when cinematic cross-dressing officially stops being funny. Sandler plays both twins of the title, and his Jill is pretty much what you would fear: just a screechingly irritating man in bad drag. Jill pulls lumps of wax out of her ears, leaves big sweaty patches on the bed, and defecates noisily after eating Mexican food. It's funny because it's a woman doing it, you see? If you had to identify the exact second of comic death, it would probably come at the close of a scene in which Jack disguises himself as Jill (so, Sandler without a wig puts on a wig) in order to seduce Al Pacino but then the melons fall out of his bra!

In 2000, the American Film Institute voted Some Like It Hot the best American comedy ever made, with Tootsie in second place, so you could say the only direction for the cross-dressing movie was downwards. But in the past decade or so, the decline has become a meteoric plummet, to the extent that drag is now the last resort of the lowest-aiming multiplex mass-market entertainer. Some of them have even made a career out of it – Martin Lawrence has three Big Momma's House films to his name; Tyler Perry's "Madea" alter-ego has appeared in seven movies. But for the majority, their comic potency shrivelled the moment they stepped into size 10 stilettos. John Travolta hasn't been taken seriously since Hairspray, Williams hasn't been funny since Mrs Doubtfire, White Chicks and The Hot Chick scotched any notion that either Shawn and Marlon Wayans or Rob Schneider were the future of comedy, and Eddie Murphy's career is only just recovering from Norbit, in which his monstrously overweight "Rasputia" helped him to an unprecedented hat-trick of Razzie awards for worst actor, worst supporting actor and worst supporting actress.

Guys dressing as girls has been a dramatic tradition long before cinema, of course. You could trace the lineage through pantomime, vaudeville, Shakespeare, Japanese Noh, Greek and Norse mythology, back to the first neanderthal who thought it would be a laugh to try on his partner's mammoth-skin scarf. But while one half of this tradition led to drag – an art form in which the performer's wit and individuality are to the fore, in which the frock isn't the whole picture – the other half has brought us to the sorry state we are in now. Admittedly, some of the screen's manliest actors have ticked with transvestite turns, including Cary Grant (I Was A Male War Bride), Michael Caine (Dressed to Kill), Arnold Schwarzenegger (Junior) and Robert De Niro (Stardust). Johnny Depp has done it twice (Ed Wood, Before Night Falls), Robert Downey Jr did it well (that is, badly) in the recent Sherlock Holmes.

But when it comes to entire films based around drag, they tend to follow a predictable pattern. It is only a matter of time before your hero/heroine is ineptly lathering on the slap and almost giving the game away by punching people or being good at sports. There will be a scene in which a dim bloke unwittingly cracks on to our star, and another in which a desirable woman takes them into intimate, sisterly confidence. But you can be sure that hetero normality will be restored by the final reel. The guy will get the girl, learn a few life lessons, and forget he ever took a walk on the wild side. And all of this depends on nobody ever seeing through the cross-dresser's subterfuge, even though it is crashingly obvious to the audience.

Cross-dressing is (or at least was) funny precisely because it plays with gender boundaries. Theorists such as Judith Butler have suggested that all gender is performative, that "male" and "female" are cultural constructs rather than biological facts, and that drag is a way of subverting these tropes. But there is little of that happening in Jack and Jill. If anything, it's the opposite. By caricaturing what is considered "unacceptable" in women, as Sandler's Jill does, these films are actually drawing thick boundaries around what really is acceptable in women – both in terms of body and behaviour. So when men posing as women do "girl things", it is invariably shopping, makeup and beauty treatments, just as we are invited to laugh at them for being fat, ugly and unladylike.

And you can bet there is a model of ideal womanhood somewhere in the film for extra contrast. Just as Norbit had Thandie Newton and Big Momma's House Nia Long, Jack and Jill has the blandly pristine Katie Holmes. As the LA Times reviewer put it, "When it comes to women in Sandler's world, he only sees extremes: hot or not, worthy of putting on a pedestal or getting hit with one."

African-American entertainers who have cross-dressed, meanwhile, have been further criticised for producing racist caricatures. Chris Rock and Spike Lee have both spoken out against Perry's Madea, and Ebony editor Jamilah Lemieux wrote in an open latter to Perry: "I just can't quite get with seeing Mother Dear played by a 6ft 3in man with prosthetic breasts flopping in the wind. Our mothers and grandmothers deserve much more than that. Heck, our fathers and grandfathers deserve more." Perry and Sandler's get-out clause would be that they are laughing at themselves, rather than at women in general. But the world isn't laughing with them any more.

If Sandler hasn't killed the transvestite comedy, though, then Work It should finish it off. This new US sitcom once again rolls out the cross-dressing cliches, on the supposedly timely but extremely shaky premise that women are now taking all the good jobs, thus forcing its male stars to drag up. "To stay employed, Lee and Angel must put aside their alpha-male selves and learn to navigate their all-female workplace," the press blurb says. You can guess the rest. Reactions to Work It have ranged from "an early front-runner for the worst show of 2012" to "a retrograde shame-spiral of a series that hates women nearly as much as its viewers will hate themselves". The show has also drawn criticism from another quarter: transgender groups. In December, the Gay and Lesbian Alliance Against Defamation (Glaad) and Human Rights Campaign took out a full-page advertisement in Variety stating that: "Work It Doesn't Work." "By encouraging the audience to laugh at the characters' attempts at womanhood, the show gives licence to similar treatment of transgender women," it reads.

"In 34 states, you can be fired for being transgender," explains Herndon Graddick, Glaad's spokesperson, "so rather than having an easier time, which is what the show ridiculously tries to portray, trans people often have a very hard time supporting themselves."

Does that mean cross-dressing in film and TV shows can't be funny any more? "One could ask the same about blackface," Graddick replies, "which has been a staple of comedy for centuries. People have a more intuitive sense of where and if that might be appropriate, and if it were to be done now, it would be with great sensitivity to the issues at play. We're not saying that you can't ever be funny about these things, obviously. But people have become more aware of all the pieces of the fabric of society, transgender people included. So Work It has the double problem of a more sophisticated audience and a less sophisticated product."

When cross-dressing is done the other way round, however, the results are generally far more revealing. Several female actors have won, or been nominated for, Oscars for male impersonations: Julie Andrews in Victor/Victoria; Linda Hunt in The Year of Living Dangerously; Hilary Swank in Boys Don't Cry; Felicity Huffman in Transamerica; even Gwyneth Paltrow in Shakespeare in Love. Corseting up to join their ranks this year are Glenn Close and Janet McTeer, who both masquerade as 19th-century chaps in Albert Nobbs.

It would be a sad conclusion that transvestism is acceptable only when taken seriously. Done well, transvestite comedies have been a great way to gently broach tricky subjects such as discrimination, gender difference and homosexuality – as with classics such as Tootsie, La Cage Aux Folles or The Adventures of Priscilla, Queen of the Desert. It's the "done well" bit that's key, though. You can get away with anything if it's funny enough. Given their propensity for making comedy out of social taboos of the lavatorial kind, you would think Sandler and co could have brought more to this party than fancy dress and fat suits. Perhaps, beneath the likes of Jill and Rasputia, lie the unrequited yearnings of our fading comics to really get in touch with their big, fat feminine sides. It's a shame none of them seems to have the balls.

• This article was amended on 27 January 2012. The original referred to "trannie comedies" in the final paragraph. This has been corrected.